I have been working with Jessica Soto Campos for a number of years to produce visuals to help explain the joy of finding thinking styles and guiding your team by a mental model Skyline representing the cognition of people you want to support. (You’ve seen Jess’ charming illustrations on my website, posts, and essays over the years.)
We recently finished this illustration which explains how my courses lead to certain outcomes for your team. Andy Polaine asked, “I enjoyed these very much. Do these sketches have several iterations or come out pretty fully formed? I’d love to see how the evolve if it’s the former.”
After a few weeks of us chatting & sketching, where Jess had the idea of the courses being an adventure to follow, “like a hiker,” I finally thought of the idea of a trail map. I sent Jessica Soto Campos some random map illustrations as an inspiration:
Jess created an initial sketch, then we worked on it over the course of several weekly working sessions, across four or five weeks, with notes to each other in between. In the first working session, Jess was sketching while I was musing aloud. Like, “People can go the mmSkyline route or the Thinking Styles route.” Or, “People need to be able to scan the whole landscape of what the org knows, and what’s going on externally, while framing a study.” I tried tying these concepts in with beautiful hiking destinations. Jess created this initial version:
In our next working session, Jess pointed out that the organization is nowhere to be seen on this map about helping organizations. I thought for a moment then suggested maybe we could make the town on a lake represent the org. She was like, “No, that is not clear. Plus there is too much going on.” She came up with the idea of a building to represent the org. And I asked to move all the trail signposts over near the org, as the things you can accomplish at the destination:
Often we work in Mural, with me adding lines in green and sticky notes on top of what Jess had sketched for the week. Mural is a great way to work, especially since we are 9 hours apart.
Then we organized those sign posts and re-worded some of them so that we could put them within reach of the org. Jess also created a Trail Map label for the whole diagram. And we cleaned up the pile of sketches that were sprinkled around the org:
Feedback from my Tuesday Team made it obvious that there was too much detail. So I simplified the course representations. A lot.
We couldn't figure out a way to show how the Practice Groups (the tents where I meet with everyone real-time) related to the self-paced online courses. Finally, I managed to sketch something that allowed the tent to look like it's on the ground, with a trail shortcutting it in front. (The Practice Groups are optional. Next one kicks off 25-March.) You can see that I was not in front of a device when I jotted down the idea! Old school blue ink pen on a notebook page! 📒🖋️
We launched the Courses Trail Map, and then I remembered another ability teams can unlock after taking only the first course, Listening Deeply. (This course is currently 25% off, code PREP4FTS.) So we added that, bringing the Outcomes to a total of seven.
I hope you enjoyed seeing the evolution!
From the text in the Trail Map, Outcomes under Listening Deeply:
Create trust relationships with stakeholders
Reduce conflict, collaborate lucidly across teams
Support team members in their career growth
Outcomes from all of the courses:
Idea camp: truly human, deeply supportive creative thinking guided by thinking styles and the selected priority from the mmSkyline
Measure people’s success at their own intentions/goals (in line with their own cognition, when most orgs tend to measure the success of the solution)
Mindfully choose strategic direction (and priorities) over the course of a decade
Mend gaps in your existing solutions, to support all types of cognition
Listening Deeply is currently 25% off (code PREP4FTS).
The Practice Group that goes with Listening Deeply kicks off 25-March-2026, and runs for six weeks. There are four price tiers, including 50% off tier if you pay your own way, without an org reimbursing you.
The all-new course Finding Thinking Styles will launch in mid May 2026, along with its associated Practice Group. (You need Listening Deeply to understand Finding Thinking Styles.)
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